p-Toluenesulfonic acid → HCID 68902439, compound

HRID 1785633Notes

Reaction equation

HRID 1785633 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:28]([N:41]1[CH2:44][CH:43](O)[CH2:42]1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[CH:28]([N:41]1[CH2:44][CH:43]([O:12][CH:4]([C:5]2[CH:6]=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=2)[C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[Cl:1])[CH2:42]1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 247332(2-Chlorophenyl)(4-chlorophenyl)methanolHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 68902439HCID 68902439, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,4′-dichlorobenzhydrol (7) (178 mmol), p-toluenesulphonic acid (198 mmol) and 1-benzhydryl-3-azetidinol (1) (99 mmol) in toluene (500 mL) was heated at reflux in a Dean-Stark apparatus for 40 minutes. The solution was cooled, washed with sodium hydrogen carbonate (saturated aqueous solution, 700 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography [SiO2; (10% ethyl acetate:isohexane)] to finish the product as a yellow oil (17.8 g, 38%).

Workup

  1. temperatureat reflux in a Dean-Stark apparatus for 40 minutes
  2. temperatureThe solution was cooled
  3. washwashed with sodium hydrogen carbonate (saturated aqueous solution, 700 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography [SiO2; (10% ethyl acetate:isohexane)]

Sources & evidence

ORD record
ord-19df17d08103449b8e050be2f961799e
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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